4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one → HCID 58844695, compound

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Reaction Conditions

Reaction Steps

Sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[3-(hydroxymethyl)phenyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (160 mg) prepared by example 4 was dissolved in DMF (2.0 ml), and thereto 4-(bromomethyl)-5-methyl-1,3-dioxol-2-one (143 mg) was added at 0° C. The mixture was stirred at 0° C. for 1 hour and then thereto ice water was added. The mixture was extracted with ethyl acetate. The organic layer was washed three times with a cold saturated aqueous sodium chloride solution, followed by a cold saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by preparative thin-layer chromatography (ethyl acetate/acetone) to give (5-methyl-2-oxo-1,3-dioxo1-4-yl)methyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[3-(hydroxymethyl)phenyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (62 mg).

Provenance & Evidence